TABLE OF CONTENTS
Trip Highlights
Tour details
Itinerary
What's included
Terrain
Condition Grading
Itinerary Changes
Starting point and getting there
Food, Weather
Gear checklist
Currency & Banking
Passports, Visas
Italy has a way of drawing you in gradually, revealing itself through layers of history, landscape, and everyday life that feel both timeless and vividly alive. It’s a country where art, food, and tradition are not separate experiences but part of a continuous cultural fabric. The rhythm shifts as you move, vibrant and energetic in the cities, slower and more contemplative in the countryside, and effortlessly relaxed along the coast. In central Italy, rolling hills lined with cypress trees, vineyards, and medieval villages create an iconic scenery shaped over centuries, while further west, the Ligurian coastline offers a striking contrast of rugged cliffs, turquoise waters, and colorful seaside towns. Over nine immersive days, this journey combines cultural highlights with active exploration, beginning in Rome before heading into the Tuscan countryside around Pienza, where a gentle hike unfolds through rolling hills and quiet rural landscapes. The journey continues through the historic streets of Siena and on to San Gimignano, where we spend one day hiking through vineyard-covered hills, olive groves, and scenic trails in the surrounding countryside, framed by the iconic medieval skyline of the town. The final stretch is spent along the dramatic coast of the Cinque Terre, based in Monterosso al Mare, with three days dedicated to hiking the coastal paths that connect its villages. From ancient landmarks to countryside trails and seaside routes, each stage of the trip offers a distinct perspective, coming together as a balanced journey through some of Italy’s most iconic and varied landscapes.
TRIP HIGHLIGHTS
- Journey through the heart of Italian history, from the monumental icons of Rome to the winding medieval alleys of Siena, where every piazza tells a story of a bygone era
- Step into a postcard-perfect landscape while hiking through sunlit vineyards and cypress-lined ridges, with San Gimignano standing proudly above the hills
- Indulge in Italy’s culinary heritage, tasting rustic dishes and fine wines crafted from the land, each reflecting the character of its region
- Get away from it all along the Cinque Terre, walking timeless coastal paths between vineyard terraces and pastel-hued villages clinging to the cliffs
TOUR DETAILS
- Days/Nights: 9 days / 8 nights
- Single supplement: Cost based on request. Availability limited.
- Condition grading: Moderate
ITINERARY
DAY 1
Arrival in Rome and welcome dinner
Your journey begins in Rome. Eternal and ever-evolving, Rome is a city where layers of history rise effortlessly into modern life. Ancient ruins stand beside bustling cafés, Renaissance palaces open onto lively piazzas, and everyday moments unfold in the shadow of monuments that have shaped the world. In the afternoon, you will meet at your hotel for a brief orientation and introduction to the journey ahead. To conclude the evening, we gather for our first dinner together at a traditional Roman restaurant, sharing local flavors and conversation as we begin to get to know one another, in quiet anticipation of the adventure that lies ahead.
Overnight in Rome
Dinner included
DAY 2
Guided tour of Rome and drive to Pienza
Today, we discover the highlights of Rome on a guided walking tour with a local expert, bringing the Eternal City to life through its most iconic landmarks. We stroll through centuries of history as we visit the Pantheon, the Colosseum, the Roman Forum, Trevi Fountain, and Capitoline Hill, among other treasures, covering approximately 4 km on foot. Along the way, ancient ruins, grand piazzas, and lively streets reveal the layered story of a city that has shaped Western civilization for millennia. After time for lunch and a final taste of Rome’s vibrant atmosphere, we depart in the afternoon and leave the city behind as we journey into the heart of Tuscany. The landscape gradually transforms from urban sprawl to rolling hills, cypress-lined roads, and open countryside as we travel toward Pienza, a Renaissance hill town set in the Val d’Orcia.
Overnight in Pienza
Breakfast and dinner included
Driving distance:
Rome to Pienza 190 km / 3 hr
DAY 3
Hike from Pienza to Bagno Vignoni
Today we set out on a full-day hike through the rolling green landscapes of Tuscany, following quiet country paths that wind between cypress trees, scattered farmhouses, wheat fields, and distant hilltop villages. Departing directly on foot from Pienza, we walk into the heart of the Val d’Orcia, a landscape shaped by centuries of agriculture and beautifully balanced between nature and human cultivation, where every ridge reveals another sweeping view. Our route leads us first toward the iconic Chapel of the Madonna di Vitaleta, standing alone among the fields, before continuing across gentle hills and open countryside toward Bagno Vignoni. Here we conclude our hike in the unique atmosphere of this historic thermal village, where warm waters fill the central square and steam rises gently from ancient stone basins that have drawn visitors since Roman times. The evening is at leisure, allowing you to explore and dine wherever you choose.
Overnight in Pienza
Breakfast and lunch included
Hiking distance: 12,8 km / Hiking duration: 4 hr
Elevation gain & loss: 228 m & 480 m
DAY 4
Transfer to San Gimignano and visit Siena on the way
Say farewell to the Val d’Orcia and set off toward Siena, a magnificent medieval city that once rivaled Florence in wealth and influence, built on centuries of banking, trade, and artistic patronage. Upon arrival, we explore the historic center on a guided visit, wandering through its atmospheric lanes and discovering highlights such as the striking Piazza del Campo, famously home to the dramatic Palio horse race held twice a year, as well as the impressive cathedral, a masterpiece of Gothic architecture and craftsmanship. In the mid-afternoon, we continue by a short drive into the heart of Tuscany to San Gimignano, a beautifully preserved hill town renowned for its medieval skyline of stone towers, once symbols of wealth and power, now rising above vineyards and olive groves in the surrounding countryside where we settle in for the next two nights. As the day winds down, we gather for dinner in a local restaurant, sharing regional dishes and a final glass of wine as the town slowly settles into its evening rhythm.
Overnight in San Gimignano
Breakfast and dinner included
Driving distance:
Pienza to Sienna 55 km / 1 hr
Sienna to San Gimignano 41 km / 50 min
DAY 5
Hike from San Gimignano to a winery
Today we set out on a scenic hike through the rolling countryside surrounding San Gimignano, leaving the town’s towers behind as we follow quiet paths through vineyards, olive groves, and open Tuscan hills. The trail unfolds through classic wine country scenery, with cypress trees and scattered farmhouses marking the rhythm of the landscape, until we arrive at a family-run organic winery nestled among the vines. Here, the hike concludes with a wine tasting experience paired with a light lunch, showcasing the estate’s wines alongside local seasonal dishes, all enjoyed in the relaxed setting of the Tuscan countryside. After returning to San Gimignano, the afternoon is left free to explore at your own pace, whether wandering its historic lanes, visiting a museum, or simply enjoying a gelato in one of its lively squares.
Overnight in San Gimignano
Breakfast and lunch included
Hiking distance: 10 km / Hiking duration: 4 hr
Elevation gain & loss: 274 m & 317 m
DAY 6
Drive to Levanto and hike to Monterosso
Leave the rolling hills of Tuscany behind as we journey toward the Ligurian coast, driving approximately three hours to Levanto, a relaxed seaside town just north of the Cinque Terre. Here, we take time to wander its laid-back streets and perhaps sample local specialties such as fresh focaccia or farinata, a traditional chickpea flatbread, before setting off on foot along the coastline. Our hike follows a scenic trail climbing above the sea toward Monterosso al Mare, the largest of the five villages and our base for the next three nights. Along the way, panoramic views open over the rugged coastline and the colorful villages perched between cliffs and sea. By late afternoon, we arrive in Monterosso, where the pace softens and, as the day visitors depart, a quieter side of the Cinque Terre begins to emerge.
Overnight in Monterosso
Breakfast and dinner included
Hiking distance: 8 km / Hiking duration: 3 hr
Elevation gain & loss: 563 m & 556 m
Driving distance:
San Gimignano to Levanto 190 km / 3hr
DAY 7
Hike from Monterosso to Corniglia
Spend the day hiking the scenic trails of the Cinque Terre, moving between its iconic villages along historic coastal paths. We begin directly from Monterosso al Mare, following a beautiful trail to Vernazza, often considered the most picturesque of the five, where there is time to wander the harbor or pause for a coffee by the sea. From here, the path continues to Corniglia, perched high above the water with sweeping coastal views and a quieter atmosphere. After some time to explore, we return to Monterosso by train. In the evening, we gather for dinner at a local restaurant, enjoying fresh regional dishes and the relaxed ambiance of the Ligurian coast.
Overnight in Monterosso
Breakfast and dinner included
Hiking distance: 10 km / Hiking duration: 4 hr
Elevation gain & loss: 700 m & 689 m
DAY 8
Hike from Corniglia to Manarola
This morning, a short train ride brings us back to Corniglia, where we resume our journey along the coast. The trail leads us high above the sea toward Manarola, crossing a landscape shaped by centuries of human effort, steep slopes carved into narrow terraces and planted with vines that seem to cling to the cliffs. The path offers sweeping views over the coastline before descending into Manarola, where there is time to pause, explore, and perhaps enjoy a gelato or a relaxed lunch by the water. After the day’s hike, we return to Monterosso al Mare by ferry, offering a different perspective of the coastline from the sea. In the evening, we gather once more for a final dinner, celebrating the journey and the landscapes we’ve explored together.
Overnight in Monterosso
Breakfast and dinner included
Hiking distance: 6,5 km / Hiking duration: 3 hr
Elevation gain & loss: 370 m & 319 m
DAY 9
Say farewell to Italy or continue your journey independently
Breakfast is at your leisure at the hotel. Following this, you will transfer independently to the nearest airport for your onward flight home, or choose to extend your stay and continue exploring Italy at your own pace, perhaps returning to a favorite city, discovering a hidden corner, or simply allowing a little more time to linger in la dolce vita.
Breakfast included
WHATS INCLUDED
Price includes:
All accommodations based on double occupancy
Hotel taxes and service charges
All transportation during the trip with a private van
All fuel, taxes, and tolls as per itinerary
Entrance fees to historic sites, museum and parks
Services of an English speaking hiking guide
Archeological guides for the visits of Rome and Sienna
All activities as mentioned in the program
Transport and handling of reasonably sized baggage
Included meals:
Breakfast, lunches and dinners as indicated in the itinerary
Not Included:
Domestic and/or international air fare
Transfer to and from the airport
Medical expenses
Travel or emergency evacuation insurance
Gratuities for leader/guide or driver
Alcoholic beverages and meals other than outlined in itinerary
Visas if needed
Other items of a personal nature
Anything not mentioned in above program
ITINERARY CHANGES
We are constantly updating our unique itineraries based on new information and experiences available. The walks, accommodations, and visits listed may be adjusted. The itineraries presented are subject to modification and change by Tripin Adventures. We reserve the right, without penalty, to make changes in the published itinerary whenever, in our judgment, conditions warrant, or if we deem it necessary for the comfort, convenience, or safety of participants, anything not mentioned in above program.
TERRAIN
This trip level is Moderate and is suitable for most people that are in fairly good physical condition. The itinerary includes walking tours in cities and villages, and five days with moderate hikes of 3-4 hours. Although the paths are quite well-kept there are some parts that the tend to be very stony and rocky. You will mostly be walking on footpaths, trails and on some tarmac roads and be prepared for few steeper passages.
CONDITION GRADING
Moderate
Trips designated "Moderate" are more active and require a bit more endurance. Hikes and treks includes occasional steep ascents. Trip members should be experienced hikers in good physical condition, capable of walking 3-5 hours
STARTING POINT AND GETTING THERE
Starting point is: Rome
Getting There: Rome is served by two airports: Fiumicino (Leonardo da Vinci), the primary international hub located about 30km southwest of the city, and Ciampino, situated 15km southeast. Rome is a global gateway connected with direct flights to numerous cities across Europe, North America, South America, Africa, and Asia..
Getting away: The tour ends in Monterosso al Mare, the largest of the Cinque Terre villages. The closest major airport is Pisa Galileo Galilei (PSA), located approximately 95km to the south. Pisa Airport serves as a significant regional hub, offering direct connections to over 80 destinations across Europe, the Middle East, and North Africa. Travelers depart from the tour independently and can reach the airport via a direct train from Monterosso to Pisa Centrale, followed by a quick 5-minute ride on the "Pisa Mover" shuttle.
FOOD
Fresh, flavorful, and delightfully simple, the sun-kissed Italian cuisine is dolce vita on the plate. It reflects the history and bounty of its diverse regions and relies on the fresh, seasonal home-grown produce and generally simple, unfussy cooking that brings out the rich flavors of the Mediterranean. The culinary journey from Rome through Tuscany to the Cinque Terre is a celebration of Italy’s varied landscapes. In Rome, the cuisine is bold and hearty, famously known as cucina povera (peasant cooking), where humble ingredients like Pecorino Romano and guanciale create world-renowned pastas. Traveling north into Tuscany, the plate shifts to the rustic abundance of the countryside, think thick, golden olive oils, earthy truffles, unsalted bread, and world-class wines from the rolling hills. Reaching the Cinque Terre, the air turns salty and the menu transforms; here, the steep terraced cliffs offer fragrant basil for the world’s finest pesto, paired with the freshest seafood caught daily from the Ligurian Sea.
WEATHER
The climate of Rome, Tuscany, and the Cinque Terre is characterized by a classic Mediterranean influence, though it varies as you move from the city to the coast. In Rome and inland Tuscany, summers are warm and sunny, with average maximum temperatures in July and August often reaching 30°C to 33°C. In the shoulder months of May, June, September, and October, the weather is particularly pleasant, with averages hovering around 22°C to 26°C. As you move toward the Cinque Terre, the Ligurian Sea provides a refreshing breeze that tempers the summer heat, though the humidity can be higher. While the coastal cliffs stay mild, the hilly terrain of the Tuscan countryside can experience cooler air in the evenings, so we recommend always having a light layer or a jacket for outdoor dinners. In addition to the sun, these regions can experience occasional Mediterranean rain showers, particularly in late spring and early autumn. The Cinque Terre, with its steep coastal topography, is especially prone to brief but intense afternoon thunderstorms, making a light waterproof shell a sensible addition to your daypack.
GEAR CHECKLIST
Base your clothing on the “layering system”, if it is hot you can “peel off” layers quickly, if it is cooler and windy you can quickly “dress up”. The lighter you travel, the easier you travel. Use your best judgement and pack as lightly as possible. You will appreciate light luggage towards the end of your trip Please consider taking along the following items on your trip.
OFFICIAL PAPERS
- Valid passport
- Airline tickets
LUGGAGE
- Duffel bag or rolling luggage
- Daypack to carry camera, water bottle and snacks etc.
- Luggage locks and tags
OUTERWEAR
- Midweight polar fleece sweater
- Rain jacket and rain pants, or poncho
CLOTHING
- Hiking shorts
- Casual clothing made of light-weight fabrics
- T-shirts
- Long-sleeve shirt
- Hiking pants, loose and easy to move in
- Underwear
- Swimsuit
CLOTHING ACCESSORIES
- Sun hat or baseball cap
FOOTWEAR
- Lightweight and supportive hiking boots, broken-in with good ankle support
- Beach sandals
- Casual, comfortable shoes for evening
ACCESSORIES
- Sunscreen and lip protection
- Sunglasses and retainer strap
- Beach towel
OPTIONAL ACCESSORIES
- Security pouch or money belt
- Trekking poles or walking staff
- Camera, memory and batteries
- Reading and writing materials
- Watch with alarm or travel alarm
- Travel pillow
- Motion sickness remedies
- Personal first-aid kit
- Insect repellent (lowrisk)
- Electric adapter plug/converter
This is not a fixed list, but more of a guideline, so feel free to add and remove items as you see fit.
CURRENCY & BANKING
Italy has adopted the Euro as its currency. The easiest way to obtain local cash is from an ATM. Greek ATMs accept cards bearing the Cirrus, EC, Euro card, Visa and Plus symbols. If you take cash, US or Canadian Dollars can be easily exchanged at banks. Most major credit cards, Visa, MasterCard and American Express are accepted. It is advisable to have some Euros with you upon arrival to be used for a taxi if necessary. You may want to check the website www.xe.com for current exchange rates.
PASSPORTS
You must have a passport valid for at least 6 months beyond the conclusion of your trip. Please make sure that you have blank pages in your passport for your visa (if required), entry and exit stamps (one for each). Please make a copy to take with you in the event yours is lost or stolen and keep it separate from your actual passport.
VISAS
Currently an Italian Tourist Visa is not required for citizens of Canada, United States, Britain and Australia. If you hold another passport, please check online http://visacentral.com/visas.php
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